17201-04-6Relevant articles and documents
The first one-pot amidation of alkanes and cycloalkanes
Akhrem, Irena S.,Avetisyan, Dzul'etta V.,Afanas'eva, Lyudmila,Vitt, Sergei V.,Petrovskii, Pavel V.,Orlinkov, Alexander
, p. 1399 - 1404 (2008)
Alkanes (or cycloalkanes) and CO in the presence of superelectrophilic systems CX4·2AlBr3 (X = Cl, Br) have been applied for the first time as equivalents of acylium salts in one-pot selective syntheses of amides from amines.
Utilizing Carbonyl Coordination of Native Amides for Palladium-Catalyzed C(sp3)?H Olefination
Park, Hojoon,Li, Yang,Yu, Jin-Quan
supporting information, p. 11424 - 11428 (2019/07/17)
PdII-catalyzed C(sp3)?H olefination of weakly coordinating native amides is reported. Three major drawbacks of previous C(sp3)?H olefination protocols, 1) in situ cyclization of products, 2) incompatibility with α-H-containing substrates, and 3) installation of exogenous directing groups, are addressed by harnessing the carbonyl coordination ability of amides to direct C(sp3)?H activation. The method enables direct C(sp3)?H functionalization of a wide range of native amide substrates, including secondary, tertiary, and cyclic amides, for the first time. The utility of this process is demonstrated by diverse transformations of the olefination products.
Low-Pressure Radical11C-Aminocarbonylation of Alkyl Iodides through Thermal Initiation
Chow, Shiao Y.,Odell, Luke R.,Eriksson, Jonas
, p. 5980 - 5989 (2016/12/26)
A radical11C-aminocarbonylation protocol characterized by excellent substrate compatibility was developed to transform alkyl iodides into11C-labelled amides, including the 11β-HSD1 inhibitor [carbonyl-11C]adamantan-1-yl(piperidin-1-yl)methanone. This protocol serves as a complementary extension of palladium-mediated11C-aminocarbonylation, which is limited to the preparation of11C-labelled compounds lacking beta-hydrogen atoms. The use of AIBN as a radical initiator and a low-pressure xenon–[11C]CO delivery unit represents a simple and convenient alternative to previous radical11C-carbonylation methodologies burdened with the need for a proprietary high pressure reactor connected to a light source.